Find Cheap Flights from Caribbean to Chicago

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Caribbean to Chicago

(Round-trip)
Depart: Mon Oct 16 2017 Return: Sat Oct 28 2017 Trip spans 13 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Fri Sep 22 2017 Return: Sun Sep 24 2017 Trip spans 3 days
American Airlines
American Airlines
SJU
ORD
5h 17m
nonstop
ORD
SJU
4h 42m
nonstop
Depart: Thu Nov 16 2017 Return: Mon Dec 4 2017 Trip spans 19 days
JetBlue
JetBlue
BGI
ORD
17h 33m
1 stop
ORD
BGI
9h 40m
1 stop
Depart: Wed Oct 18 2017 Return: Wed Oct 25 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Thu Nov 2 2017 Return: Tue Nov 7 2017 Trip spans 6 days
Frontier
Frontier
SJU
ORD
15h 00m
1 stop
ORD
SJU
14h 41m
1 stop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
United
United
MBJ
ORD
4h 25m
nonstop
ORD
MBJ
7h 21m
1 stop
Depart: Fri Oct 20 2017 Return: Sat Oct 28 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Wed Nov 29 2017 Return: Mon Dec 4 2017 Trip spans 6 days
JetBlue
JetBlue
NAS
ORD
12h 15m
1 stop
ORD
NAS
9h 48m
1 stop
Depart: Fri Sep 29 2017 Return: Mon Oct 30 2017 Trip spans 32 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Fri Sep 22 2017 Return: Tue Sep 26 2017 Trip spans 5 days
American Airlines
American Airlines
SJU
ORD
8h 17m
1 stop
ORD
SJU
7h 49m
2 stops
Depart: Thu Dec 7 2017 Return: Wed Dec 13 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
15h 00m
1 stop
ORD
SJU
14h 30m
1 stop
Depart: Sun Oct 15 2017 Return: Sat Oct 28 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Frontier
Frontier
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Wed Sep 27 2017 Return: Fri Oct 6 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
4h 40m
nonstop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
United
United
MBJ
ORD
4h 25m
nonstop
ORD
MBJ
7h 21m
1 stop
Depart: Mon Oct 16 2017 Return: Wed Oct 18 2017 Trip spans 3 days
American Airlines
American Airlines
POS
ORD
28h 41m
1 stop
ORD
POS
13h 13m
2 stops
Depart: Mon Oct 16 2017 Return: Mon Oct 23 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 33m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 31m
1 stop
ORD
SJU
14h 41m
1 stop
Depart: Sun Sep 24 2017 Return: Mon Sep 25 2017 Trip spans 2 days
JetBlue
JetBlue
SJU
ORD
6h 49m
1 stop
ORD
SJU
6h 41m
1 stop
Depart: Thu Oct 12 2017 Return: Tue Oct 24 2017 Trip spans 13 days
Multiple Airlines
Multiple Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
12h 32m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Aguadilla
$247
Bridgetown
$268
Nassau
$288
San Juan
$255
Montego Bay
$343
Piarco
$320
Destination

Chicago
$247
Airlines Airline reviews

14 travelers who booked a flight from Aguadilla to Chicago rated their chosen airlines with an average of 7.9.

Overall
8.6
Boarding
8.1
Crew
8.4
Comfort
8.1
Food
7.0
Entertainment
7.4